


Stiles is in need of advice

by juliehei



Category: Teen Wolf (TV)
Genre: Awkward Conversations, Blow Jobs, Bottom Stiles, First Time, Knotting, M/M, Mating, Porn With Plot, Rimming, awkward moments
Language: English
Status: Completed
Published: 2013-04-13
Updated: 2013-04-13
Packaged: 2017-12-08 09:52:37
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 3,531
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/760018
Author URL: https://archiveofourown.org/users/juliehei/pseuds/juliehei
Summary: <blockquote class="userstuff">
              <p>Stiles seeks advice on how to properly seduce a werewolf from the only other person he knows about that is currently dating one</p><p>or</p><p>The first time Stiles picks up his courage and does something about the sexual tension between him and Derek.</p>
            </blockquote>





	Stiles is in need of advice

**Author's Note:**

> Please, be gentle with me. This is my first fanfiction and English is not my native tongue. However I do appreciate all advice you could give me before my next one! This is not beta'd, so I hope there are no major mistakes that I have overlooked in it. I hope you will enjoy it nevertheless :)

Stiles needed help, serious amounts of help. Or advices, whatever you would like to call it. There were two persons who could give him the advices he needed, one was the first love of his life the other was the only love of his bestfriends life. How the hell was he supposed to ask sex advices from those two women? Why did werewolf sex have to be so difficult?

Stiles kind of figured Allison would be the best choice because her boyfriend was actually a werewolf, while Lydia’s was only part werewolf part lizard. So he called Allison up and his brain to mouth filter shut down, yet again. “I need advice on how to properly seduce and fulfill a werewolf’s sexual desires.” The other end of the line was completely silent for so long that he actually had to pull his phone away from his head to make sure she hadn’t hung up on him. “Is it Erica?” Allison sounded terrified of the idea that Stiles would like to do Erica. “Ehm, no. It’s a male werewolf to be frank with you. Actually a more exact term yet again may be a male, alpha werewolf…”

“I’m coming over in twenty minutes. You are going to the store to buy condoms and lube and be back before I am.” Well, he really hoped she wasn’t giving him a demonstration because he was painfully aware he only liked guys. Well, guys and Lydia’s brain. After he turned fifteen and Lydia’s body didn’t arouse him anymore, he just adjusted “in love with Lydia” to “in love with Lydia’s brain”.

Oh, shit! Had it already passed five minutes since Allison hung up? He needed to get to the store right now, because he was not being late for this. Not in a million years would he miss being educated about how to properly arouse a werewolf.

 

***

 

Stiles was sitting in his car outside Derek’s apartment. He was painfully aware of the supplies resting in his backpack and his growing boner who was only reacting to his expectations about the night. There was no fooling Derek though, he already knew Stiles was there and that he would come up at any moment. One deep breath and Stiles was out the car door and headed for the stairs up to Derek’s apartment. He took three steps at a time and was slightly breathless when he reached the top floor. The door was unlocked as usual. Derek could hear anyone coming from miles in each direction, so why would he lock the door when he was home?

Stiles let himself in and bucked of his shoes and his outer jacket in the hall before he found his way into the living room. “What do you want now, Stiles?” Derek didn’t even turn his head away from the TV to look at him. In Stiles’ fantasies, this was because he couldn’t stand to look at him without trying to jump him. But that was off course in Stiles’ fantasies only. Derek probably couldn’t stand to look at him all together. That was why Allison’s master plan of seduction was needed to get Derek to drop his pants to the floor for Stiles.

Step 1 in this master plan was to lightly touch the werewolf’s neck with step 2 only following if you still had your hand attached to your arm. Stiles dropped his backpack halfway across the living room and came up right behind the sofa Derek was sitting on. “I just wondered about something... I’ve done some research on the matter… Would you just…” Stiles stopped talking in the same moment his hand touched Derek neck and he stopped breathing. Then Derek was making a sound deep in his throat that sounded frighteningly animalistic and turned Stiles on even more. 

He decided that step 1 was a success and moved on to Step 2. Slowly kissing, breathing and very carefully biting at Derek’s neck. Thank god for werewolf strength, because a regular human being could never have thrown Stiles over the back of the sofa and into Derek’s lap without hurting one of them. Step 3, what the hell was step 3 again?

It was touching. Light touches all over his body until Derek was supposed to be begging for Stiles’ hands on other parts of his anatomy. Stiles let his hands roam freely over Derek’s broad chest and muscular arms while continuing working his lips all over Derek’s neck. The noises coming out of Derek was much louder, making him sound more like an animal with every syllable he uttered. 

Stiles moved around in Derek’s lap to find a more comfortable position when he noticed the bulk in Derek’s pants currently pressing against his ass. Wait, this had something to do with step 4. Damn, he should have persuaded Allison into making these steps more easy to remember, so that he could come up with them even when his hands and mouth were occupied. Step 4 was touching Derek down there. Stiles, being Stiles, was hit by a wave of insecurity.

Derek was obviously enjoying Stiles’ mouth at his neck and Stiles’ hands roaming all over his upper body, but did he want Stiles’ hands near his junk? Stiles settled for a thing in the middle when he dragged Derek’s shirt up and tickled his fingers along the waistband of his boxers. Derek responded with increasing the volume of his moans and bucking his hips up to meet Stiles’ hand.

Okay, this is a fantastic idea, now step 5 is to kiss him on the mouth. Allison said to make it filthy but to watch out for fangs. “Derek would probably be able to keep from hurting you on purpose, but you just might hurt yourself on those badboys once or twice,” were her exact words. Stiles wanted to make this as perfect as he could, so with his normal amount of elegance he twisted in Derek’s lap so he could straddle it with one knee on each side.

Bad move. When his dick aligned with Derek’s, no matter that there were many layers of clothes between them, Stiles’ brain short-circuited and he forgot why he moved. Derek’s eyes also shot open and he was staring into the pair opposite his for way to long. They decided it was time for movement at the same time. Their mouths crashing together at the same moment as Derek grabbed Stiles’ ass and grinded his hips up against him. 

Among moans and barks of pleasure Derek actually managed to make a short sentence. “This is much more comfortable in the bedroom, Stiles.” Stiles on the other hand, had forgotten how to form words, so he settled on only grunting an approving sound hoping Derek would understand. Derek did understand and suddenly Stiles was lifted into his strong arms and carried towards the door leading to Derek’s bedroom. 

He remembered something Allison had told him about her needing some extra lubricant with Scott and that Stiles would probably be needing even more than her. “Backpack…” he muttered into Derek’s mouth before he continued kissing him and tightening his legs around Derek’s waist. “I know exactly what you have in that backpack, and I have plenty of it in my bedside drawer. Don’t worry.” 

Off course, werewolf senses. Wait, Derek was prepared for this? For sex with someone else? Somehow Stiles was sure Derek could read his mind sometimes. “I have wanted you since the first time I slung you into a wall, and you have not stopped pushing yourself into my space ever since.” Oh my god, Derek had wanted him even longer than Stiles had wanted Derek. Oh holy shit. Derek chose that exact moment to press soft kisses and small bites into Stiles’ neck and he had nothing to say to Derek’s announcement. 

“Your sent is intoxicating, do you know that? And the only thing I can think about when you bend over in front of me is how fuckable that ass of yours is…” Every other word was punctuated with a nip of Derek’s teeth at Stiles’ neck. Who knew Derek was a dirty talker. If Stiles didn’t have a neck full of lovebites tomorrow he would be surprised. 

Stiles wanted to touch more of Derek’s skin, preferably now at once. He started clawing and dragging at Derek’s shirt to get it of him. Derek wasn’t helping at all. He had his own agenda going on down at Stiles’ belt buckle. His hand was faster than lightning when he finally got the damn thing open. Stiles was sure it only took him a second from it was open until his boxers was out of the way and Derek had one hand firmly around his fully hard dick. 

“You know, had I known this was a sure way to shut you up completely, I would have done this a long time ago.” Somehow, Derek’s bullying was the thing that sent Stiles back to life and booted up his brain again. He knew what he wanted, Derek was on board with it and his hand was currently covering the base of Stiles’ cock. “If you really want me to shut up for good, you need to do more than just hold around it and whisper nasty things in my ear.”

Stiles was more secure in his movements this time around when he went for Derek’s shirt. Stiles was happy it was off, but he wasn’t as happy about Derek removing his hand from his dick to take it off. The disappointment won out and Stiles made a sound that only embarrassed him. Derek decided he would keep Stiles waiting a little longer and stood to remove his own trousers before he went back to touching Stiles.

“Oh, that is so good” Stiles couldn’t help it. His brain to mouth filter had vanished long ago (read: somewhere in kindergarten, but for the moment being we pretend it was when Derek first grabbed a hold of him on the sofa), but his mouth only started working again the second Derek’s hand stroked his cock. “Obviously there’s more I can do to shut you up because this isn’t working.” Oh, the expression on Derek’s face was nothing short of naughty. He started slowly kissing down Stiles’ neck towards his navel. He took a sidetrip though and bit down on one nipple which made Stiles moan so load he was afraid the neighbors could hear him if the walls weren’t thick enough. When Derek’s mouth reached his navel and his tongue came out to play with it, Stiles’ hips buckled upward and gave his dick a very brief contact with Derek’s bare skin. 

“Oh, so you want my mouth little longer south, do you? I can do that.” Out of nowhere, Derek’s mouth covered the whole length of Stiles’ cock and his breath got totally stuck in his throat. How had he survived more than 17 years without a blowjob? This was nothing close to him rubbing one out in the shower, with lube, after sitting on his hand or any of them combined even. This was a thousand times better and Derek hadn’t done anything but swallowed him whole once.

At least Stiles thought this was a thousand’s times better, but that was until Derek started moving and it became a million times better. Stiles was only slightly aware that his hips was moving in sync with Derek’s head and that his hand was probably pulling a little too hard on Derek’s hair. But what he hell, this is a werewolf, there was nothing he could do to really hurt him. 

Stiles had only ever managed to keep his focus on two things at once. Right now number one was Derek’s mouth around his dick and number two was whether or not Stiles was hurting him when he pulled at his hair. That is why the first inkling of an orgasm hit him like lightning from a blue sky. He only had time to utter Dereks name and a short “I’m cumming” to warn him. But Derek didn’t move away, he started sucking at it even harder and swallowed the whole load without blinking.

Stiles had tasted his own juice before, but it was something much more arousing about tasting himself of off Dereks tongue. “I came here with supplies for something a lot more exciting than that. But since I’m in no shape to fuck you, would you please fuck me now?” There was his lack of brain to mouth filter again, Stiles was afraid for a moment that Derek wouldn’t do what he asked him to. However that was before he was flipped around, propped up on his knees and felt a long stroke of something wet and puffy over his asshole.

Oh god, Derek was rimming him. Stiles felt the tip of Dereks tongue working around his tight muscle before it disappeared completely. Actually, Derek’s weight disappeared from the bed completely for a while, before his tongue was back working at Stiles’ ass. Derek gave no warning about the first finger, he just pushed it in and kept his tongue working around it. 

Stiles did get a warning before the second finger and for the two after that. Stiles was a whimpering mess beneath Dereks cunning hand and perfect tongue before ten second had gone by. Every time Derek hit his prostate, which was nine out of ten trusts of his fingers, Stiles buckled down into the mattress and moaned. He was fully hard again after almost 15 minutes off assplay and was growing restless. Derek had four fingers up his ass by this point, he should really be ready for Derek’s dick by now.

“I swear to god, if you don’t put your dick in me soon I will hunt you down and shoot you with Allisons crossbow” Derek only quickened the pace of his fingers and put his mouth just by Stiles’ ear to whisper back; “You are ready when I say you are, but right now I am enjoying watching you squirm and beg for me to give you what you want.” Derek grabbed Stiles’ neck to pull it backwards, making Stiles arch his back so that his ass was still rutting against Derek’s hand. “But you are very close Stiles, do you really want me to fuck your ass?”

“Yes, please Derek. I need you now. My cock is all hard for you again, just shove yours up my ass NOW!” The last word was a shout and a moan in one. Derek had started not only brushing past Stiles’ prostate, but actively massaging it. Stiles was on the verge of cumming again and was actually prepared for it when Derek pulled his hand out and aligned his dick with Stiles’ crack. “Are you ready for me, Stiles?”

Stiles wasn’t sure how to answer such a question, so instead he leaned forward until his head hit the mattress and pulled his cheeks away from each other to give Derek a better view. This time around, it was Derek’s turn to moan. “Oh shit, Stiles. You look so good and ready.” He pushed slowly in and even though it did hurt a little, the pleasure of it overrode the pain in Stiles’ mind. “Oh god, You feel even better…”

When Derek was finally fully inside of Stiles, he could let a breath of relief spill out of him. He experimentally squeezed and flexed is hole to see what reactions he could get out of Derek and the responding moan of pleasure was all he wanted. Derek didn’t seem ready to move just yet, still adjusting to the new heat around his dick, but Stiles had waited too long to have patience with him. Stiles started moving slightly forward and then just as slowly moving back to let the whole length of Derek in again.

That was obviously just the right thing to do because it made Derek start to move as well. And Stiles had been right. Derek was just as turned on as he was. After a few trusts Derek had nailed in the position of Stiles’ prostate again and was giving of growls that by far drowned Stiles’ already loud moans. Stiles didn’t know why, but Derek’s hand is snaking around his body to wrap itself around his cock again.

It only takes Derek five trusts of his hand before Stiles is cumming once again. Not far after him is Derek. With the most animalistic howl yet he’s pushing in one last time to empty himself in Stiles’ soothing heat…

But he isn’t moving out again and Stiles can feel Derek’s dick growing instead of slacking off as his just did. “Ehm, Derek, shouldn’t you be pulling out about now?” There is cursing behind him and Stiles starts to become a little afraid of not knowing what is actually happening in his ass right now. “Stiles, I need you not to panic. If you move right now it might be very painful for both of us.” At the words “not panic”, Stiles automatically freezes his body into a statue, there is no way he can stand any pain right now.

“There is this thing male werewolves do when they are pairing with their mate. The base of their cock grows so that they trap their spunk inside the female to increase the chance of them conceiving a child. I think that just happened to me.” If there was one thing Stiles had always been proud of it was his ability to tackle problems at a moment’s notice and being able to find a bright side to any situation. Right now he had nothing to say, nothing to say what so ever.

“So does that mean that I am your mate? What does that mean for me?” Derek stiffened behind him and it caused a very small movement of his hips. Stiles whimpered, this time in pain. He did not want Derek to move again. In an effort to make sure Derek didn’t rustle anything still inside of Stiles he tried to lean into it and it actually helped just a little bit.

“It doesn’t necessary mean anything for you at all, you are not a wolf. I have expected that you were my mate for a long time, but I didn’t for sure before the moment you started scenting my neck on the sofa because of the feelings you aroused. For me, this means I will never find someone I want more than you. I can’t chose anyone but you, but you can chose anyone you want” Derek sounded a little pained. Like the thought of having to share Stiles with anyone was the worst thing that could happen to him right now. Somehow Stiles felt that the right thing to do was to keep asking questions so that he could properly understand the situation that he was currently in. That thought made him laugh kind of hysterically. He had an enlarged version of Derek’s dick stuck in his ass and he was planning out the rest of his life as a werewolf’s mate. This was seriously fucked up.

“Was something I said funny?” This tone was completely different from the one Derek used just moments ago. This was afraid and maybe even a little hurt that Stiles could laugh in a moment like this. “Relax, it was nothing you said. It’s just that I was seriously considering spending the rest of my life in your arms and the thought actually didn’t put me off at all. Then I remembered that I still had your cock stuck in my ass and the whole situation was kind of funny to me.”

When Stiles stopped talking, he noticed that Derek had actually stopped breathing all together. What the hell had he just said that could make the brooding and scary Derek Hale hold his breath? Then it dawned on Stiles, he had absolutely nothing against living the rest of his life in Derek’s arms! They were actually kind of perfect together if he thought about it, constantly opposing each other but always coming to the right conclusion together in the end. If the wolf in Derek had chosen him, Stiles was more than happy to choose the human in Derek as his.

It seemed like holding his breath made Derek able to shrink his penis back to regular size a little faster, because just a few moments after Stiles had figured out he would spend the rest of his life with Derek, he pulled out and pinned Stiles into a hug. “Did you seriously just say that you would be happy to spend the rest of your life in my arms? Be with me forever? Seriously?”

Stiles couldn’t help himself for laughing a little at Derek. “Dude, you just sounded like a puppy, or maybe even Scott at his worst. Yes, I would like to spend a lifetime in your arms, and more importantly I would prefer it if we are naked in at least one third of that time period.” Now Derek was laughing as well, hugging Stiles even tighter than before. 

“I love you.”


End file.
